The best executive summaries methodically “tell a story” about a compelling vision, using facts and data to make that story convincing. Think of an executive summary as the pick-up line and brief conversation leading to a first date, NOT a full courtship and marriage proposal – so keep it concise and linear (excess data/content really only makes it confusing, like a 65-page PowerPoint). Consider extensive use of headings, sub-headings, and bullet points; content should be cohesive and intuitively organized – carefully apply small doses of narrative to manage/influence the reader’s thought process from start to finish. Personally, I typically use a disciplined outline that flows as follows: Business Model, Marketing, Operations, Management, and Finance:

Business Model – Just a few sentences, concisely describing (1) who you are, (2) what you do, and (3) why the reader should care, followed by (4) a blunt description of how you make money. This segment must be absolutely clear and unambiguous – it is the single most important item that will entice your reader to continue, and sets the conceptual foundation for everything else they will read.

Marketing – Industry and market overview (third-party research to validate the opportunity). What is the nature/scope of the opportunity? Strategy/positioning: what do you sell, who do you sell it to, and why do they buy from you? Standard writing style, flowing from broad to specific (industry overview, segment stats, target market, competitive commentary, customer profile, specific products, etc.).

Operations – How does the business actually work? What are the most critical elements? Not the gory details, just the fundamental construct. Here, you want to shape the reader’s “mental model” of your business. You want them thinking “OK, I get it – that’s doable”.

Management – What best qualifies this team to execute the business model/strategy (kicking the snot out of every other competing team)?

Finance – What is your financing roadmap; how much do you need, what exactly will you use it for, and what might your investors expect in return? You really need to focus on cash flow, and describe specific sources/uses. Cash flow is the most critical early-stage variable.

Now for random trivia:

Cater to the Audience – Sophisticated investors think almost exclusively in terms of minimizing risk and maximizing reward. The only reason they are reading your summary is to assess those variables, so write with their interests in mind. In their heads, confusion and complexity = risk. Make the path to reward obvious, lest they accidentally get lost along the way.

Write in Third Person – A subtle trick; always write in the third-person (never say “our, we, I”; always say “the Company”, “management”, etc.). It sounds inherently more credible, as if an impartial journalist wrote the summary. Footnote cited facts as you reference them; objectively academic and convincing.